FR2207707A1 - 2-Pyrrolidone-5-carboxylic acid esters and amides - with sedative and hypnotic activity - Google Patents

2-Pyrrolidone-5-carboxylic acid esters and amides - with sedative and hypnotic activity

Info

Publication number
FR2207707A1
FR2207707A1 FR7242163A FR7242163A FR2207707A1 FR 2207707 A1 FR2207707 A1 FR 2207707A1 FR 7242163 A FR7242163 A FR 7242163A FR 7242163 A FR7242163 A FR 7242163A FR 2207707 A1 FR2207707 A1 FR 2207707A1
Authority
FR
France
Prior art keywords
pyrrolidone
carboxylic acid
sedative
amides
acid esters
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
FR7242163A
Other languages
French (fr)
Other versions
FR2207707B1 (en
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pierre Fabre SA
Original Assignee
Pierre Fabre SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Pierre Fabre SA filed Critical Pierre Fabre SA
Priority to FR7242163A priority Critical patent/FR2207707A1/en
Publication of FR2207707A1 publication Critical patent/FR2207707A1/en
Application granted granted Critical
Publication of FR2207707B1 publication Critical patent/FR2207707B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06139—Dipeptides with the first amino acid being heterocyclic
    • C07K5/06173—Dipeptides with the first amino acid being heterocyclic and Glp-amino acid; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
    • C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D207/28—2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Title cpds. of formula (where R is -O.CH2.CCl3, -O.CH2.CBr3, -NH.CH.CCl3, -NH,CH2.CO2R' where R' is H or alkyl) and their acid-addn salts of the free bases, are prepd. by reaction of 2-pyrrolidone-5-carboxylic acid chloride with the appropriate alcohol or amine R.H. The cpds. are suitable for oral, parenteral or rectal administration. the oral LD50 in mice varies from 1780 to >5000 mg/kg. The ED50 in the Rota-rod test is 422 to 1700 mg/kg orally.
FR7242163A 1972-11-27 1972-11-27 2-Pyrrolidone-5-carboxylic acid esters and amides - with sedative and hypnotic activity Granted FR2207707A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR7242163A FR2207707A1 (en) 1972-11-27 1972-11-27 2-Pyrrolidone-5-carboxylic acid esters and amides - with sedative and hypnotic activity

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7242163A FR2207707A1 (en) 1972-11-27 1972-11-27 2-Pyrrolidone-5-carboxylic acid esters and amides - with sedative and hypnotic activity

Publications (2)

Publication Number Publication Date
FR2207707A1 true FR2207707A1 (en) 1974-06-21
FR2207707B1 FR2207707B1 (en) 1975-11-28

Family

ID=9107796

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7242163A Granted FR2207707A1 (en) 1972-11-27 1972-11-27 2-Pyrrolidone-5-carboxylic acid esters and amides - with sedative and hypnotic activity

Country Status (1)

Country Link
FR (1) FR2207707A1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2270867A1 (en) * 1974-05-14 1975-12-12 Hoechst Ag
EP0314275A2 (en) * 1987-08-20 1989-05-03 Kissei Pharmaceutical Co., Ltd. 2-Pyrrolidone-5-carboxylic acid compounds

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3051722A (en) * 1960-10-21 1962-08-28 Lakeside Lab Inc 5-pyrrolidone-2-carboxamides

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3051722A (en) * 1960-10-21 1962-08-28 Lakeside Lab Inc 5-pyrrolidone-2-carboxamides

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2270867A1 (en) * 1974-05-14 1975-12-12 Hoechst Ag
EP0314275A2 (en) * 1987-08-20 1989-05-03 Kissei Pharmaceutical Co., Ltd. 2-Pyrrolidone-5-carboxylic acid compounds
EP0314275A3 (en) * 1987-08-20 1991-07-31 Kissei Pharmaceutical Co., Ltd. 2-pyrrolidone-5-carboxylic acid compounds

Also Published As

Publication number Publication date
FR2207707B1 (en) 1975-11-28

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Legal Events

Date Code Title Description
ST Notification of lapse